Cheap flights from Orlando to Chicago from $105

The month of February is, on average, the cheapest month to fly to Chicago from Orlando, with most prices found around $170. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Orlando to Chicago during January average around $173.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $325. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Orlando to Chicago for around $545.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Orlando to Chicago during this time can be as low as $254. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $552.

Fly from Orlando Sanford Intl to Chicago Greater Rockford for the best Orlando - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Orlando when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $254 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Orlando for as low as $217 on momondo.

There are 4 cabin classes available to choose from on Orlando to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between Orlando to Chicago.

As of September 2026, prices for Orlando to Chicago flights are approximately 85% more expensive when compared to flights at the same time last year.

United Airlines, JetBlue, and Southwest are the most popular carriers operating from Orlando to Chicago

Frontier, American Airlines and United Airlines are the top three most popular airlines that fly to Chicago from Orlando according to our data. Frontier is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 18% of flights between Orlando and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 145 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 9% of their flights experiencing any sort of delay.

As of September 2026, there are 52 flights per day flying from Orlando to Chicago. The most common time of day flights depart is 8:00AM, with 51% of flights taking off in the afternoon.

As of September 2026, 370 flights take off from Orlando and land in Chicago each week. The most common flight departure day for this route is Sun, with 19% of weekly flights taking off on this day.